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All posts Subject: salycilic acid to anthranillic acid ? Please login to post

xxxxx
(Stranger)
04-24-04 16:16
No 502690
      salycilic acid to anthranillic acid ?

phenol does not react with ammonia to form aniline. resorcinol does react with ammonia at 140C to form meta hydroxy aniline. phlorglucinol reacts with ammonia at room temperature to form 3,5 dihydroxy aniline (maybe a second hydroxyl group could be replaced by heating to 140C).
   this is because the ketonic tautomer becomes more predominant because of conjugation, and it is the ketonic tautomer which reacts with the ammonia.
   in salycilic acid the carbonyl group has a carbon oxygen double bond in position to conjugate with the hydroxyl carbon. could this increase the ketonic tautomer of the hydroxyl group to the point where it could be replaced with an amine group? is there any literature which gives the ratio of keto to enol for the hydroxyl group in salycilic acid, and is it more or less than resorcinol?

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	All posts		Subject: salycilic acid to anthranillic acid ?		Please login to post


		xxxxx (Stranger) 04-24-04 16:16 No 502690				salycilic acid to anthranillic acid ?
						phenol does not react with ammonia to form aniline. resorcinol does react with ammonia at 140C to form meta hydroxy aniline. phlorglucinol reacts with ammonia at room temperature to form 3,5 dihydroxy aniline (maybe a second hydroxyl group could be replaced by heating to 140C). this is because the ketonic tautomer becomes more predominant because of conjugation, and it is the ketonic tautomer which reacts with the ammonia. in salycilic acid the carbonyl group has a carbon oxygen double bond in position to conjugate with the hydroxyl carbon. could this increase the ketonic tautomer of the hydroxyl group to the point where it could be replaced with an amine group? is there any literature which gives the ratio of keto to enol for the hydroxyl group in salycilic acid, and is it more or less than resorcinol?

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